NPASS Compound

Natural Product: NPC6377

Natural Product ID	NPC6377
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Momordin I
IUPAC Name	(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1608255
PubChem CID	44202126
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 118124 0 0 0 0 0 0 0 0999 V2000 3.6034 1.6144 3.9023 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8678 1.7155 3.3323 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4138 2.8440 3.3597 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4912 0.5168 2.7380 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6846 -0.5747 2.8487 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0053 -0.9605 1.7215 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1927 0.0783 1.3117 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8556 -0.2433 1.2465 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0107 0.4354 2.3007 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4672 0.1992 2.0514 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7764 1.0257 0.7750 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0924 0.2408 -0.2721 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3804 0.0117 -0.1533 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6939 -1.2554 -0.9369 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1917 1.1005 -0.8267 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4938 0.5893 -1.6680 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9711 0.2341 -1.7585 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8108 1.0966 -0.7996 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2567 0.9308 0.5491 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0148 1.8603 1.4868 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3809 1.3025 1.4866 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9646 0.7719 0.4528 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2509 0.6997 -0.8299 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3962 -0.6027 -1.5602 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0984 1.6531 -1.6996 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5214 1.2004 -1.7111 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1824 0.9275 -0.4207 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3549 0.2639 0.6308 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4880 -1.1969 0.7997 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6395 -1.8664 0.1515 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1950 -3.2539 -0.3480 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7583 -2.1742 1.1607 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2704 -1.1987 -1.0069 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4940 0.2322 -0.7115 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6090 2.2784 0.1232 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4106 3.3503 -0.4561 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2594 2.2831 1.3468 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7068 2.4761 -1.3992 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3208 2.3917 1.0754 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0003 -1.3068 0.6418 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1951 -0.4140 0.5842 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9122 0.8537 1.3334 C 0 0 2 0 0 0 0 0 0 0 0 0 7.1200 1.5536 1.4161 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6502 -0.1769 -0.7118 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9252 -0.6757 -0.9047 C 0 0 2 0 0 0 0 0 0 0 0 0 8.8521 0.3274 -1.1534 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8872 -0.0462 -1.9833 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4066 -1.3956 -1.5438 C 0 0 1 0 0 0 0 0 0 0 0 0 9.3408 -2.4044 -1.9700 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9728 -1.7265 -1.9914 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0263 -2.6959 -1.7164 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6520 -2.8200 -3.2558 O 0 0 0 0 0 0 0 0 0 0 0 0 11.6077 -1.6549 -2.1867 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4136 -2.6356 0.9068 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1497 2.3828 4.3902 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4504 0.2980 3.2963 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4305 -1.8946 1.9240 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8054 -1.3351 1.5468 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2274 -0.0137 3.2961 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3091 1.4794 2.3481 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0028 0.5899 2.9086 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5972 -0.8813 1.8598 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5357 -0.8090 -0.1357 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1720 -2.0178 -0.2864 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7769 -1.7444 -1.3199 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4384 -1.0780 -1.7501 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9522 1.5245 -0.1047 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6069 1.9099 -1.2450 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8233 0.7156 -1.6728 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2064 1.5431 -2.0607 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0079 -0.1775 -2.3461 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9979 -0.7926 -1.3472 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2602 0.3474 -2.8036 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5302 -0.1022 0.8835 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5531 1.8851 2.4922 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9402 2.8741 1.0877 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9059 1.3648 2.4633 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0834 -0.3981 -2.6033 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8516 -1.4561 -1.1951 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4549 -0.9267 -1.6720 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0905 2.6780 -1.3416 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7924 1.6423 -2.7600 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6618 0.4230 -2.5081 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0843 2.0712 -2.1901 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7639 0.6744 1.6163 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5364 -1.7476 0.5366 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5651 -1.5118 1.8974 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1122 -3.8753 -0.4292 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8324 -3.1359 -1.4111 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4181 -3.6942 0.2746 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7699 -2.0395 0.6866 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6320 -1.4984 2.0219 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7134 -3.2053 1.5282 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7720 -1.4123 -1.9686 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2985 -1.6626 -1.1346 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1177 0.3133 0.2007 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9833 0.7974 -1.5330 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2271 3.0969 1.9772 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2349 3.2630 -0.8767 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9580 2.3496 -2.4784 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6424 2.8401 -1.5008 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6939 2.6716 0.8204 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9837 3.2285 0.7195 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3995 2.5677 2.1970 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5164 -1.3667 -0.3629 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0259 -0.9489 1.1166 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2059 1.5217 0.8104 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1555 2.2637 0.7289 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2960 -1.1767 0.0395 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6903 0.7246 -1.9389 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5805 -0.1262 -3.0386 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5911 -1.4349 -0.4436 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3244 -3.2151 -1.2292 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7713 -1.2738 -2.9837 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9783 -3.3743 -2.4153 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8332 -2.0003 -3.7959 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2335 -0.9159 -2.0660 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3106 -2.5784 1.3072 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 13 15 1 0 12 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 1 6 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 30 32 1 0 30 33 1 0 33 34 1 0 27 35 1 1 35 36 2 0 35 37 1 0 18 38 1 6 11 39 1 1 6 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 41 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 49 52 1 0 48 53 1 0 40 54 1 0 42 4 1 0 50 45 1 0 13 8 1 0 23 18 1 0 34 27 1 0 19 11 1 0 28 22 1 0 1 55 1 0 4 56 1 1 6 57 1 1 8 58 1 1 9 59 1 0 9 60 1 0 10 61 1 0 10 62 1 0 12 63 1 1 14 64 1 0 14 65 1 0 14 66 1 0 15 67 1 0 15 68 1 0 15 69 1 0 16 70 1 0 16 71 1 0 17 72 1 0 17 73 1 0 19 74 1 1 20 75 1 0 20 76 1 0 21 77 1 0 24 78 1 0 24 79 1 0 24 80 1 0 25 81 1 0 25 82 1 0 26 83 1 0 26 84 1 0 28 85 1 1 29 86 1 0 29 87 1 0 31 88 1 0 31 89 1 0 31 90 1 0 32 91 1 0 32 92 1 0 32 93 1 0 33 94 1 0 33 95 1 0 34 96 1 0 34 97 1 0 37 98 1 0 38 99 1 0 38100 1 0 38101 1 0 39102 1 0 39103 1 0 39104 1 0 40105 1 6 41106 1 1 42107 1 6 43108 1 0 45109 1 1 47110 1 0 47111 1 0 48112 1 1 49113 1 1 50114 1 6 51115 1 0 52116 1 0 53117 1 0 54118 1 0 M END

Standard InCHIKey	HWYBGIDROCYPOE-UDXSKONJSA-N
Standard InCHI	InChI=1S/C41H64O13/c1-36(2)14-16-41(35(49)50)17-15-39(6)20(21(41)18-36)8-9-24-38(5)12-11-25(37(3,4)23(38)10-13-40(24,39)7)52-34-29(46)30(28(45)31(54-34)32(47)48)53-33-27(44)26(43)22(42)19-51-33/h8,21-31,33-34,42-46H,9-19H2,1-7H3,(H,47,48)(H,49,50)/t21-,22-,23-,24+,25-,26-,27+,28-,29+,30-,31-,33-,34+,38-,39+,40+,41-/m0/s1
SMILES	OC(=O)[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)CC[C@@]2([C@H]3CC(C)(C)CC2)C(=O)O)C)C)[C@@H]([C@H]([C@@H]1O)O[C@@H]1OC[C@@H]([C@@H]([C@H]1O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	764.43	Volume:	764.16 ? Van der Waals volume.
Dense:	1.0	LogP:	2.674 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.825 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.15 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	40.0
TPSA:	212.67 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	7.0	Rings:	7.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.152	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.736	Fsp³:	0.902
MCE-18:	152.308 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.951	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.019 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.184	Promiscuous compounds:	0.119

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.95	MDCK Permeability:	-5.177
Pgp-inhibitor:	0.0	Pgp-substrate:	0.009
PAMPA:	1.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.048	30% Bioavailability (F30%):	0.026
50% Bioavailability (F50%):	0.721

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.994
Plasma Protein Binding (PPB):	79.463%	Volume Distribution (VD):	-0.588
Fu:	14.334% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.46	BCRP inhibitor:	0.0
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.004	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.149 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

0.293

Half-life (T1/2):

2.454

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.003
Human Hepatotoxicity (H-HT):	0.778	Drug-induced Liver Injury (DILI):	0.971
AMES Toxicity:	0.551	Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.02	Skin Sensitization:	0.999
Carcinogencity:	0.335	Eye Corrosion:	0.0
Eye Irritation:	0.025	Respiratory Toxicity:	0.191
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.982
Hematotoxicity:	0.657	Drug-induced Nephrotoxicity:	0.99
Genotoxicity:	0.75	RPMI-8226 Immunitoxicity:	0.037
A549 Cytotoxicity:	0.132	Hek293 Cytotoxicity:	0.066
BCF:	0.521 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.52 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.082 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.236 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO11459	Parmelia formosana	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1620	Dictyopteris prolifera	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO773	Siphonaria maura	Species	Chytriomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15071	Lissoclinum perforatum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7500	Rhodiola algida	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9554	Parthenium ligulatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10387	Mandragora vernalis	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7500	Rhodiola algida	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7500	Rhodiola algida	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11459	Parmelia formosana	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO773	Siphonaria maura	Species	Chytriomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8494	Pteris longipes	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8750	Lychnis githago	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6196	Aralia armata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10387	Mandragora vernalis	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10972	Lysimachia patungensis	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7500	Rhodiola algida	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3067	Frullania nisquallensis	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1620	Dictyopteris prolifera	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10373	Senna pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9554	Parthenium ligulatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15071	Lissoclinum perforatum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Potency	29
IC50	4
AC50	4
Ratio IC50	1
CC50	1

Activity Type	# Activity
Individual protein	24
Cell line	2
Protein complex	2
Others	11

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	20596.2	nM	PubChem BioAssay data set
NPT198	Individual protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	79432.8	nM	PubChem BioAssay data set
NPT135	Individual protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	56234.1	nM	PubChem BioAssay data set
NPT199	Individual protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	79432.8	nM	PubChem BioAssay data set
NPT154	Individual protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	3162.3	nM	PubChem BioAssay data set
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	3662.6	nM	PubChem BioAssay data set
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	14581.0	nM	PubChem BioAssay data set
NPT101	Individual protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	28183.8	nM	PubChem BioAssay data set
NPT159	Individual protein	Aberrant vpr protein	Human immunodeficiency virus 1	Potency	n.a.	5623.4	nM	PubChem BioAssay data set
NPT160	Individual protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	35481.3	nM	PubChem BioAssay data set
NPT199	Individual protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	42284.1	nM	PubChem BioAssay data set
NPT11	Individual protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	44668.4	nM	PubChem BioAssay data set
NPT9	Individual protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	50118.7	nM	PubChem BioAssay data set
NPT917	Individual protein	Dengue virus type 2 NS3 protein	Dengue virus type 2 (strain Thailand/16681/1984) (DENV-2)	IC50	n.a.	30960.0	nM	PubChem BioAssay data set
NPT919	Individual protein	HSP90	Plasmodium falciparum 3D7	AC50	=	1057.0	nM	PubChem BioAssay data set
NPT446	Individual protein	Rap guanine nucleotide exchange factor 3	Homo sapiens	Potency	n.a.	50118.7	nM	PubChem BioAssay data set
NPT921	Protein complex	c-Myc/Max	Homo sapiens	IC50	=	4000000.0	nM	DOI[10.1039/C2MD00289B]
NPT8	Individual protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	17782.8	nM	PubChem BioAssay data set
NPT918	Individual protein	Heat shock protein HSP 90-alpha	Homo sapiens	AC50	=	649.0	nM	PubChem BioAssay data set
NPT478	Individual protein	Ataxin-2	Homo sapiens	Potency	n.a.	11220.2	nM	PubChem BioAssay data set
NPT861	Individual protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	18356.4	nM	PubChem BioAssay data set
NPT920	Individual protein	Alpha-synuclein	Homo sapiens	Potency	n.a.	22387.2	nM	PubChem BioAssay data set
NPT62	Individual protein	6-phospho-1-fructokinase	Trypanosoma brucei	Potency	n.a.	37933.0	nM	PubChem BioAssay data set
NPT64	Individual protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	29081.0	nM	PubChem BioAssay data set
NPT74	Individual protein	Proto-oncogene c-JUN	Homo sapiens	IC50	=	30000.0	nM	DOI[10.1039/C2MD00289B]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell line	HepG2	Homo sapiens	Potency	n.a.	3548.1	nM	PubChem BioAssay data set
NPT189	Cell line	Vero	Chlorocebus aethiops	CC50	n.a.	36820.0	nM	PubChem BioAssay data set
NPT22752	Protein complex	Transcription factor AP1	Homo sapiens	IC50	=	130000.0	nM	PMID[24831826]
NPT2	Others	Unspecified	n.a.	AC50	=	2855.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	23109.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	29092.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	AC50	=	5144.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	28183.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	14125.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	11220.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	18356.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	7943.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Ratio IC50	>	100.0	n.a.	DOI[10.1039/C2MD00289B]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC6377 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	21753
0.1-0.2	24451
0.2-0.3	2488
0.3-0.4	713
0.4-0.5	333
0.5-0.6	68
0.6-0.7	34
0.7-0.8	1
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC208381
0.8452	Intermediate Similarity	NPC283849
0.8352	Intermediate Similarity	NPC114441
0.764	Intermediate Similarity	NPC286347
0.7614	Intermediate Similarity	NPC28198
0.7614	Intermediate Similarity	NPC476123
0.74	Intermediate Similarity	NPC481082
0.74	Intermediate Similarity	NPC164419
0.7363	Intermediate Similarity	NPC100383
0.7143	Intermediate Similarity	NPC488561
0.703	Intermediate Similarity	NPC104400
0.703	Intermediate Similarity	NPC10320
0.7	Intermediate Similarity	NPC469945
0.6989	Remote Similarity	NPC242611
0.6848	Remote Similarity	NPC606107
0.6733	Remote Similarity	NPC22956
0.6667	Remote Similarity	NPC166422
0.6667	Remote Similarity	NPC294112
0.6667	Remote Similarity	NPC79718
0.6634	Remote Similarity	NPC472949
0.66	Remote Similarity	NPC56713
0.6571	Remote Similarity	NPC73829
0.6542	Remote Similarity	NPC324875
0.6542	Remote Similarity	NPC292677
0.6538	Remote Similarity	NPC180550
0.6538	Remote Similarity	NPC35405
0.6535	Remote Similarity	NPC127056
0.6514	Remote Similarity	NPC11242
0.6481	Remote Similarity	NPC477193
0.6422	Remote Similarity	NPC477194
0.6364	Remote Similarity	NPC280941
0.6364	Remote Similarity	NPC235772
0.63	Remote Similarity	NPC270667
0.6228	Remote Similarity	NPC219180
0.6211	Remote Similarity	NPC204407
0.62	Remote Similarity	NPC480938
0.6154	Remote Similarity	NPC488516
0.614	Remote Similarity	NPC323341
0.6139	Remote Similarity	NPC164194
0.6132	Remote Similarity	NPC114304
0.6087	Remote Similarity	NPC251263
0.6082	Remote Similarity	NPC177246
0.6075	Remote Similarity	NPC159309
0.6075	Remote Similarity	NPC86222
0.6019	Remote Similarity	NPC136877
0.6	Remote Similarity	NPC284807
0.6	Remote Similarity	NPC276093
0.5962	Remote Similarity	NPC174679
0.5962	Remote Similarity	NPC25605
0.5962	Remote Similarity	NPC279554
0.5962	Remote Similarity	NPC59804
0.5955	Remote Similarity	NPC120840
0.5946	Remote Similarity	NPC477191
0.5932	Remote Similarity	NPC4749
0.5909	Remote Similarity	NPC488515
0.5909	Remote Similarity	NPC119794
0.5905	Remote Similarity	NPC109079
0.5893	Remote Similarity	NPC477192
0.5877	Remote Similarity	NPC477196
0.5868	Remote Similarity	NPC161717
0.5856	Remote Similarity	NPC114484
0.5818	Remote Similarity	NPC257468
0.5789	Remote Similarity	NPC477195
0.5752	Remote Similarity	NPC488209
0.5738	Remote Similarity	NPC471385
0.5714	Remote Similarity	NPC54636
0.57	Remote Similarity	NPC31839
0.5673	Remote Similarity	NPC127853
0.5652	Remote Similarity	NPC477197
0.5631	Remote Similarity	NPC191410
0.5614	Remote Similarity	NPC488564
0.5593	Remote Similarity	NPC471384
0.5593	Remote Similarity	NPC133818
0.5577	Remote Similarity	NPC475472
0.5565	Remote Similarity	NPC475486
0.5534	Remote Similarity	NPC473538
0.5526	Remote Similarity	NPC75318
0.5517	Remote Similarity	NPC62725
0.5505	Remote Similarity	NPC80843
0.5492	Remote Similarity	NPC21691
0.547	Remote Similarity	NPC288205
0.547	Remote Similarity	NPC51465
0.5444	Remote Similarity	NPC480946
0.5444	Remote Similarity	NPC130577
0.5444	Remote Similarity	NPC142415
0.5444	Remote Similarity	NPC102683
0.5431	Remote Similarity	NPC187290
0.5421	Remote Similarity	NPC12288
0.5391	Remote Similarity	NPC301449
0.5391	Remote Similarity	NPC601290
0.5385	Remote Similarity	NPC480937
0.5364	Remote Similarity	NPC482746
0.5321	Remote Similarity	NPC480424
0.531	Remote Similarity	NPC139044
0.531	Remote Similarity	NPC471383
0.5283	Remote Similarity	NPC475611
0.5254	Remote Similarity	NPC480939
0.5254	Remote Similarity	NPC480936
0.5229	Remote Similarity	NPC309780
0.5217	Remote Similarity	NPC270768
0.5217	Remote Similarity	NPC59263
0.5217	Remote Similarity	NPC210106
0.5217	Remote Similarity	NPC484832
0.5208	Remote Similarity	NPC96580
0.5189	Remote Similarity	NPC480943
0.5172	Remote Similarity	NPC37134
0.5156	Remote Similarity	NPC302543
0.5138	Remote Similarity	NPC603870
0.5135	Remote Similarity	NPC157868
0.5128	Remote Similarity	NPC323359
0.5106	Remote Similarity	NPC298554
0.5104	Remote Similarity	NPC296164
0.5083	Remote Similarity	NPC476992
0.5054	Remote Similarity	NPC275809
0.5045	Remote Similarity	NPC173583

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC6377 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6610
0.1-0.2	2496
0.2-0.3	36
0.3-0.4	6
0.4-0.5	1
0.5-0.6	0
0.6-0.7	0
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7113	Intermediate Similarity	NPD8295	Clinical (unspecified phase)

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data