NPASS Compound

Natural Product: NPC292663

Natural Product ID	NPC292663
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WPWWZJOMLDEMLW-PFYJWDNZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101425822
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 105110 0 0 0 0 0 0 0 0999 V2000 2.9353 3.4808 -3.2867 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4874 2.2369 -3.9860 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3207 2.5456 -5.4534 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4556 1.0930 -3.8385 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6506 0.6448 -2.4353 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4327 0.6527 -1.5693 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0338 -0.8162 -1.3923 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9054 -0.9853 -0.4506 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3254 -0.3169 -1.0193 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8583 -1.2739 -2.0806 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0432 1.0098 -1.5661 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0361 1.8788 -1.7344 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4555 1.5807 -1.3946 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6045 0.3468 -0.5885 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8657 0.3113 0.2594 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0463 1.4175 1.2072 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9894 0.3524 -0.7818 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3256 0.0256 -0.2562 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4246 -1.1477 0.6303 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2237 -1.4530 1.4694 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1971 -2.9892 1.5918 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4264 -3.3085 2.2154 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4428 -0.9864 2.8917 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3914 -1.2271 3.7408 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9264 -1.0616 0.8669 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7614 -1.2278 1.7762 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5273 -1.3646 0.8714 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3642 -0.0959 0.0956 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7660 0.9087 1.0371 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5098 -0.9239 1.5055 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1628 -0.1673 -1.3857 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3142 1.4957 -1.9816 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1727 1.7053 -3.4780 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9099 1.0506 -0.2051 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5400 2.0515 0.4136 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8567 0.2330 0.4442 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3492 0.5511 1.7323 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9117 -0.5117 2.6829 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8550 -0.6838 3.8456 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2379 -0.9324 3.3125 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5000 -0.2709 1.9925 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5272 -1.2842 0.8514 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3835 -2.3270 1.2579 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6940 0.8039 1.7214 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1503 -0.5127 4.2982 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4664 -1.8287 4.5436 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6644 -0.1736 3.2185 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0746 4.1372 -3.0328 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5842 4.1052 -3.9681 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5428 3.3012 -2.3878 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8770 3.4631 -5.7364 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6793 1.7401 -6.1133 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2454 2.7193 -5.7180 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4211 1.4467 -4.2854 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0997 0.2733 -4.4965 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4758 1.2946 -2.0089 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1318 -0.3677 -2.4874 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9432 -1.2931 -0.9210 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9282 -1.2362 -2.3824 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1950 -0.6418 0.5376 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6741 -2.0646 -0.3767 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5455 -2.0330 -1.6897 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0084 -1.8436 -2.5421 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3312 -0.7267 -2.9187 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8222 2.8882 -2.1451 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9647 1.5046 -2.4068 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9140 2.5000 -0.9684 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8059 -0.4743 -1.3554 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5553 2.3448 0.9353 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1492 1.6768 1.2310 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7972 1.2090 2.2662 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7020 -0.4123 -1.5515 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0237 1.3250 -1.3038 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7598 0.9487 0.2282 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7613 -2.0308 0.0135 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1196 -3.4400 0.5883 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4208 -3.3437 2.2616 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1357 -3.4612 1.5516 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7878 0.0584 2.9530 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3093 -1.6023 3.2759 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6630 -1.4965 4.6579 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7520 -1.7719 -0.0001 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6012 -0.4109 2.5065 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7626 -2.1722 2.3690 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 -2.2767 0.3074 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6542 -1.4716 1.5607 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0538 0.4027 1.7544 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1673 1.6973 0.5419 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4858 1.4241 1.6846 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1230 -0.2378 1.1333 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8879 0.4789 -2.0943 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4051 2.5145 -1.5477 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4193 2.4693 -3.6762 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9553 0.7579 -3.9893 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8429 1.5088 2.0503 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7818 -1.5074 2.2121 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8174 0.1736 4.5442 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4348 -2.0295 3.1895 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5563 0.1278 2.0433 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0046 -0.8504 -0.0512 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5330 -1.6310 0.5746 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0309 -2.5746 0.5727 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6943 -0.0233 5.0289 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9988 -2.6229 4.2812 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3006 -0.9485 3.7110 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 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 6 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 20 23 1 0 23 24 1 0 20 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 1 19 30 1 0 18 31 1 0 11 32 1 0 32 33 1 0 6 34 1 1 34 35 2 0 34 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 41 44 1 0 40 45 1 0 39 46 1 0 38 47 1 0 33 2 1 0 44 37 1 0 32 6 1 0 28 9 1 0 28 14 1 0 25 15 1 0 1 48 1 0 1 49 1 0 1 50 1 0 3 51 1 0 3 52 1 0 3 53 1 0 4 54 1 0 4 55 1 0 5 56 1 0 5 57 1 0 7 58 1 0 7 59 1 0 8 60 1 0 8 61 1 0 10 62 1 0 10 63 1 0 10 64 1 0 12 65 1 0 13 66 1 0 13 67 1 0 14 68 1 6 16 69 1 0 16 70 1 0 16 71 1 0 17 72 1 0 17 73 1 0 18 74 1 1 19 75 1 6 21 76 1 0 21 77 1 0 22 78 1 0 23 79 1 0 23 80 1 0 24 81 1 0 25 82 1 6 26 83 1 0 26 84 1 0 27 85 1 0 27 86 1 0 29 87 1 0 29 88 1 0 29 89 1 0 30 90 1 0 31 91 1 0 32 92 1 1 33 93 1 0 33 94 1 0 37 95 1 1 38 96 1 6 39 97 1 1 40 98 1 6 41 99 1 1 42100 1 0 42101 1 0 43102 1 0 45103 1 0 46104 1 0 47105 1 0 M END

Standard InCHIKey	WPWWZJOMLDEMLW-PFYJWDNZSA-N
Standard InCHI	InChI=1S/C36H58O11/c1-31(2)10-12-35(30(45)47-29-27(43)26(42)25(41)22(16-37)46-29)13-11-33(4)19(20(35)14-31)6-7-23-32(3)15-21(40)28(44)36(17-38,18-39)24(32)8-9-34(23,33)5/h6,20-29,37-44H,7-18H2,1-5H3/t20-,21+,22+,23+,24+,25+,26-,27+,28-,29-,32+,33+,34+,35-/m0/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@H]([C@@H](C(CO)(CO)[C@@H]5CC[C@@]34C)O)O)[C@@H]2C1)C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	666.4	Volume:	671.293 ? Van der Waals volume.
Dense:	0.993	LogP:	1.402 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.899 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.605 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	33.0
TPSA:	197.37 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	8.0	Rings:	6.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.156	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.552	Fsp³:	0.917
MCE-18:	130.783 ? 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:	0.899	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.014 ? 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:	0.189	Promiscuous compounds:	0.119

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.067	MDCK Permeability:	-5.106
Pgp-inhibitor:	0.0	Pgp-substrate:	0.06
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):	0.713
20% Bioavailability (F20%):	0.9	30% Bioavailability (F30%):	0.984
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.874	MRP1:	0.105
Plasma Protein Binding (PPB):	70.32%	Volume Distribution (VD):	-0.321
Fu:	25.113% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.955	BCRP inhibitor:	0.049
BSEP inhibitor:	0.224

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.005	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.411	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.491
HLM stability:	0.001 ? 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):

0.956

Half-life (T1/2):

2.843

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.013
Human Hepatotoxicity (H-HT):	0.601	Drug-induced Liver Injury (DILI):	0.121
AMES Toxicity:	0.66	Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.044	Skin Sensitization:	0.999
Carcinogencity:	0.647	Eye Corrosion:	0.0
Eye Irritation:	0.009	Respiratory Toxicity:	0.043
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.99
Hematotoxicity:	0.546	Drug-induced Nephrotoxicity:	0.972
Genotoxicity:	0.14	RPMI-8226 Immunitoxicity:	0.071
A549 Cytotoxicity:	0.09	Hek293 Cytotoxicity:	0.088
BCF:	1.367 ? 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:	3.718 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.397 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.504 ? 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
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20013	Teucrium hyrcanicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17087	Plagiomnium affine	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17087	Plagiomnium affine	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20013	Teucrium hyrcanicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26650	Terminalia chebula	Species	Combretaceae	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

Molecular-level activity

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

In vitro activity

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

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 NPC292663 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	20207
0.1-0.2	24175
0.2-0.3	4134
0.3-0.4	946
0.4-0.5	231
0.5-0.6	97
0.6-0.7	57
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8101	Intermediate Similarity	NPC199457
0.8	Intermediate Similarity	NPC68419
0.7778	Intermediate Similarity	NPC604133
0.775	Intermediate Similarity	NPC237503
0.7722	Intermediate Similarity	NPC167383
0.7229	Intermediate Similarity	NPC306746
0.7222	Intermediate Similarity	NPC150400
0.7108	Intermediate Similarity	NPC116794
0.7059	Intermediate Similarity	NPC271138
0.6988	Remote Similarity	NPC605954
0.6966	Remote Similarity	NPC29069
0.6941	Remote Similarity	NPC310014
0.6941	Remote Similarity	NPC269315
0.686	Remote Similarity	NPC102914
0.686	Remote Similarity	NPC110139
0.686	Remote Similarity	NPC108709
0.6854	Remote Similarity	NPC214484
0.6818	Remote Similarity	NPC209894
0.6782	Remote Similarity	NPC220984
0.6774	Remote Similarity	NPC295371
0.6774	Remote Similarity	NPC473884
0.6744	Remote Similarity	NPC7870
0.6744	Remote Similarity	NPC75747
0.6703	Remote Similarity	NPC48499
0.6596	Remote Similarity	NPC39211
0.6559	Remote Similarity	NPC235405
0.6559	Remote Similarity	NPC139894
0.6559	Remote Similarity	NPC475516
0.6489	Remote Similarity	NPC249848
0.6489	Remote Similarity	NPC107966
0.6436	Remote Similarity	NPC96641
0.6436	Remote Similarity	NPC163183
0.6421	Remote Similarity	NPC157868
0.6364	Remote Similarity	NPC48249
0.6354	Remote Similarity	NPC473343
0.6354	Remote Similarity	NPC469946
0.6327	Remote Similarity	NPC10607
0.6327	Remote Similarity	NPC46665
0.6304	Remote Similarity	NPC90856
0.6289	Remote Similarity	NPC192791
0.6289	Remote Similarity	NPC223301
0.6289	Remote Similarity	NPC242840
0.6289	Remote Similarity	NPC171544
0.6289	Remote Similarity	NPC112352
0.6282	Remote Similarity	NPC136313
0.6275	Remote Similarity	NPC481030
0.6263	Remote Similarity	NPC475591
0.6263	Remote Similarity	NPC236870
0.6263	Remote Similarity	NPC235438
0.6224	Remote Similarity	NPC30735
0.62	Remote Similarity	NPC222580
0.617	Remote Similarity	NPC475208
0.6162	Remote Similarity	NPC40775
0.6162	Remote Similarity	NPC251768
0.6162	Remote Similarity	NPC159309
0.6162	Remote Similarity	NPC86222
0.6146	Remote Similarity	NPC473373
0.6117	Remote Similarity	NPC80986
0.61	Remote Similarity	NPC63159
0.6078	Remote Similarity	NPC281148
0.6078	Remote Similarity	NPC104372
0.6067	Remote Similarity	NPC37739
0.6047	Remote Similarity	NPC191763
0.604	Remote Similarity	NPC297263
0.6023	Remote Similarity	NPC46388
0.6	Remote Similarity	NPC473459
0.5926	Remote Similarity	NPC475899
0.5922	Remote Similarity	NPC114484
0.5905	Remote Similarity	NPC31838
0.5905	Remote Similarity	NPC187290
0.59	Remote Similarity	NPC109588
0.59	Remote Similarity	NPC309714
0.5882	Remote Similarity	NPC609763
0.5865	Remote Similarity	NPC301449
0.5865	Remote Similarity	NPC601290
0.5842	Remote Similarity	NPC102439
0.5833	Remote Similarity	NPC179434
0.5824	Remote Similarity	NPC137917
0.5824	Remote Similarity	NPC212968
0.5818	Remote Similarity	NPC100639
0.5806	Remote Similarity	NPC256798
0.5789	Remote Similarity	NPC189884
0.5789	Remote Similarity	NPC138334
0.578	Remote Similarity	NPC481031
0.5755	Remote Similarity	NPC481078
0.5743	Remote Similarity	NPC104071
0.5728	Remote Similarity	NPC475504
0.5714	Remote Similarity	NPC65590
0.5714	Remote Similarity	NPC125923
0.5686	Remote Similarity	NPC11551
0.566	Remote Similarity	NPC241909
0.5652	Remote Similarity	NPC187056
0.5652	Remote Similarity	NPC606216
0.5652	Remote Similarity	NPC607023
0.561	Remote Similarity	NPC481361
0.5567	Remote Similarity	NPC1046
0.5566	Remote Similarity	NPC481079
0.5556	Remote Similarity	NPC75287
0.5545	Remote Similarity	NPC79643
0.5534	Remote Similarity	NPC480475
0.5521	Remote Similarity	NPC47063
0.5474	Remote Similarity	NPC128925
0.5464	Remote Similarity	NPC204458
0.5455	Remote Similarity	NPC76972
0.5455	Remote Similarity	NPC469782
0.5455	Remote Similarity	NPC204414
0.5446	Remote Similarity	NPC135904
0.5446	Remote Similarity	NPC123199
0.5432	Remote Similarity	NPC246708
0.5405	Remote Similarity	NPC192600
0.5398	Remote Similarity	NPC475160
0.5398	Remote Similarity	NPC470218
0.5398	Remote Similarity	NPC473714
0.5392	Remote Similarity	NPC475171
0.5385	Remote Similarity	NPC293330
0.5385	Remote Similarity	NPC65105
0.537	Remote Similarity	NPC295823
0.537	Remote Similarity	NPC174720
0.537	Remote Similarity	NPC475467
0.537	Remote Similarity	NPC480474
0.5326	Remote Similarity	NPC285576
0.5319	Remote Similarity	NPC64106
0.5315	Remote Similarity	NPC300419
0.531	Remote Similarity	NPC155410
0.5306	Remote Similarity	NPC238935
0.5306	Remote Similarity	NPC269095
0.5304	Remote Similarity	NPC481080
0.5294	Remote Similarity	NPC298034
0.5294	Remote Similarity	NPC71065
0.5283	Remote Similarity	NPC31193
0.5259	Remote Similarity	NPC476068
0.5253	Remote Similarity	NPC78046
0.525	Remote Similarity	NPC478657
0.5243	Remote Similarity	NPC263756
0.5243	Remote Similarity	NPC471547
0.5243	Remote Similarity	NPC213674
0.5238	Remote Similarity	NPC305267
0.5234	Remote Similarity	NPC134835
0.5229	Remote Similarity	NPC480473
0.521	Remote Similarity	NPC481081
0.5196	Remote Similarity	NPC58448
0.5192	Remote Similarity	NPC75417
0.5185	Remote Similarity	NPC73318
0.5179	Remote Similarity	NPC60557
0.5179	Remote Similarity	NPC67857
0.5172	Remote Similarity	NPC487505
0.5169	Remote Similarity	NPC41061
0.5169	Remote Similarity	NPC227551
0.5169	Remote Similarity	NPC258617
0.5143	Remote Similarity	NPC471548
0.513	Remote Similarity	NPC471550
0.513	Remote Similarity	NPC191827
0.5126	Remote Similarity	NPC43550
0.5096	Remote Similarity	NPC161674
0.5094	Remote Similarity	NPC473401
0.5093	Remote Similarity	NPC64715
0.5083	Remote Similarity	NPC135849
0.5083	Remote Similarity	NPC305981
0.5047	Remote Similarity	NPC68175
0.5044	Remote Similarity	NPC475287
0.5043	Remote Similarity	NPC480419
0.5041	Remote Similarity	NPC261506
0.5041	Remote Similarity	NPC4328

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC292663 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7102
0.1-0.2	1978
0.2-0.3	67
0.3-0.4	2
0.4-0.5	1
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
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
		NPD

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