NPASS Compound

Natural Product: NPC137887

Natural Product ID	NPC137887
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	NVTLDVSBUJGIAD-QHBXHTPSSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	71664720
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

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 104112 0 0 0 0 0 0 0 0999 V2000 -7.3564 -1.6295 -1.0930 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0209 -1.5682 -0.7974 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1356 -1.9418 -1.7851 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5295 -2.3658 -3.0315 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8907 -2.4226 -3.3155 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8017 -2.0566 -2.3525 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1474 -2.1192 -2.6523 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2748 -2.8515 -4.5736 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6290 -2.7417 -4.0253 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5134 -1.1320 0.5077 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5113 -0.6084 1.4663 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8563 -0.1697 2.7451 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4557 0.2711 2.5948 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7711 0.6947 3.6988 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4534 1.1200 3.6093 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7981 1.1228 2.3783 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4820 0.6971 1.2630 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8037 0.6981 -0.0549 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6465 -0.2276 -0.1020 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8506 -1.5691 0.1353 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2216 -2.4614 0.1058 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5035 -2.0483 -0.1562 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7208 -0.7068 -0.3957 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1244 -0.2407 -0.6660 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6828 -0.7970 -1.9124 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9162 -0.7242 -3.0806 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4428 -1.2454 -4.2345 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6856 -1.8332 -4.2912 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3979 -1.8806 -3.1208 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9322 -1.3718 -1.9010 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7273 -1.4667 -0.7640 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4315 -0.6116 0.3132 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0349 -1.2100 1.5296 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9095 -2.5576 1.7893 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4738 -3.1260 2.9360 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1625 -2.3428 3.8201 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2984 -0.9941 3.5774 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7316 -0.4472 2.4339 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0016 -0.2265 4.4912 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7221 -2.9365 4.9682 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3431 -4.4911 3.1928 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9855 -0.3798 0.5428 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8894 0.7637 1.3782 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1993 -2.3577 -5.4839 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6419 -0.1294 -3.0567 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6511 0.1621 -0.3632 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8353 1.5185 -0.5997 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2029 2.2824 -1.1795 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2214 3.7040 -1.1485 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8055 4.1745 0.0071 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2221 5.4836 0.1081 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0473 6.3416 -0.9786 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4610 5.8568 -2.1289 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0367 4.5393 -2.2440 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2979 6.7254 -3.1931 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4565 7.6615 -0.9040 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8062 5.9519 1.2648 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5229 2.0894 -0.4953 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5063 2.6090 -1.3387 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5816 -2.9047 -0.1919 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1262 -2.0645 0.4092 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7935 0.2799 1.3855 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5100 -0.1509 0.2884 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4880 1.5323 2.2105 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3387 0.7278 4.9677 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5212 -1.5445 1.7585 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1431 -1.3605 -0.4124 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0699 -1.8964 -1.5606 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7650 -2.7632 -2.1583 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9440 -3.6640 -5.0357 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8943 -3.4685 -4.6740 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0209 -2.0437 0.9727 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0347 0.2524 0.9906 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9803 -0.9138 3.5621 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4278 0.7414 3.0966 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8902 1.4599 4.4674 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5246 0.2703 -0.8182 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0485 -3.5041 0.2923 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0287 0.8728 -0.8459 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8242 -1.1752 -5.1280 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3955 -2.3386 -3.1064 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9146 0.3842 0.1337 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3636 -3.2168 1.1023 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8536 0.6103 2.2703 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6356 -0.6613 5.1385 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6965 -3.9268 5.0925 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4485 -5.1732 2.4301 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6326 -1.2131 1.2236 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4289 0.6046 2.1696 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8600 -1.7664 -5.9919 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4321 0.6492 -3.6480 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2551 1.9906 -2.2571 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9490 3.5270 0.8580 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4222 4.1419 -3.1318 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9700 6.7759 -3.9318 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8210 8.3878 -1.2357 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2547 6.5334 1.8743 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5165 2.7643 0.4087 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9708 3.3820 -0.9830 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6110 -3.8090 -0.6228 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3482 -2.3340 1.3599 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3207 0.9851 2.4127 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6085 1.6263 5.3755 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3379 -1.0834 2.0987 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 5 8 1 0 4 9 1 0 2 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 37 39 1 0 36 40 1 0 35 41 1 0 32 42 1 0 42 43 1 0 28 44 1 0 26 45 1 0 23 46 2 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 2 0 50 51 1 0 51 52 2 0 52 53 1 0 53 54 2 0 53 55 1 0 52 56 1 0 51 57 1 0 48 58 1 0 58 59 1 0 22 60 1 0 20 61 1 0 17 62 2 0 62 63 1 0 16 64 1 0 14 65 1 0 11 66 1 0 6 1 1 0 63 10 1 0 62 13 1 0 58 18 1 0 46 19 1 0 54 49 1 0 42 24 1 0 30 25 1 0 38 33 1 0 1 67 1 0 3 68 1 0 7 69 1 0 8 70 1 0 9 71 1 0 10 72 1 1 11 73 1 6 12 74 1 0 12 75 1 0 15 76 1 0 18 77 1 6 21 78 1 0 24 79 1 6 27 80 1 0 29 81 1 0 32 82 1 6 34 83 1 0 38 84 1 0 39 85 1 0 40 86 1 0 41 87 1 0 42 88 1 1 43 89 1 0 44 90 1 0 45 91 1 0 48 92 1 6 50 93 1 0 54 94 1 0 55 95 1 0 56 96 1 0 57 97 1 0 58 98 1 1 59 99 1 0 60100 1 0 61101 1 0 64102 1 0 65103 1 0 66104 1 0 M END

Standard InCHIKey	NVTLDVSBUJGIAD-QHBXHTPSSA-N
Standard InCHI	InChI=1S/C45H38O21/c46-15-7-18(48)30-29(8-15)64-42(13-3-24(54)37(60)25(55)4-13)39(62)34(30)32-20(50)11-21(51)33-35(40(63)43(66-45(32)33)14-5-26(56)38(61)27(57)6-14)31-19(49)10-17(47)16-9-28(58)41(65-44(16)31)12-1-22(52)36(59)23(53)2-12/h1-8,10-11,28,34-35,39-43,46-63H,9H2/t28-,34-,35+,39-,40-,41+,42+,43+/m0/s1
SMILES	c1c(cc(c(c1O)O)O)[C@@H]1[C@H](Cc2c(cc(c([C@@H]3c4c(cc(c([C@@H]5c6c(cc(cc6O[C@H](c6cc(c(c(c6)O)O)O)[C@H]5O)O)O)c4O[C@H](c4cc(c(c(c4)O)O)O)[C@H]3O)O)O)c2O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	914.19	Volume:	847.006 ? Van der Waals volume.
Dense:	1.079	LogP:	0.511 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.038 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.939 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	51.0
TPSA:	391.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	21.0
H-Bond Donor:	18.0	Rings:	9.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.11	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.546	Fsp³:	0.2
MCE-18:	203.333 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.872	Fluc inhibitor:	0.167 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.136 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.512 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.664	Promiscuous compounds:	0.301

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-8.13	MDCK Permeability:	-4.731
Pgp-inhibitor:	0.0	Pgp-substrate:	0.005
PAMPA:	0.986 ? 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):	0.012
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.999
Plasma Protein Binding (PPB):	85.471%	Volume Distribution (VD):	0.255
Fu:	16.671% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.023
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.995	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.0 ? 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):

2.722

Half-life (T1/2):

7.924

ADMET: Toxicity

hERG Blockers:	0.121	hERG Blockers (10um):	0.987
Human Hepatotoxicity (H-HT):	0.929	Drug-induced Liver Injury (DILI):	0.996
AMES Toxicity:	0.187	Rat Oral Acute Toxicity:	0.207
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.0	Eye Corrosion:	0.0
Eye Irritation:	0.225	Respiratory Toxicity:	0.923
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.001
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.001
A549 Cytotoxicity:	1.0	Hek293 Cytotoxicity:	0.991
BCF:	0.889 ? 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:	3.472 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.7 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.009 ? 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
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Fruit	n.a.	n.a.	DOI[10.1016/S0963-9969(99)00095-2]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	Aerial parts	n.a.	n.a.	PMID[10395493]
NPO15442	Magnolia sieboldii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11534769]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	n.a.	fruit	n.a.	PMID[16417304]
NPO14284	Delphinium shawurense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20351801]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[36557810]
NPO15442	Magnolia sieboldii	Species	Magnoliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[8988596]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3949	Ceramium rubrum	Species	Ceramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15442	Magnolia sieboldii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7713	Euplotes raikovi	Species	Euplotidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2458	Aconitum violaceum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12982	Dysidea amblia	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14673	Lathyrus nissolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6347	Iryanthera paraensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11912	Peltogyne porphyrocardia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10887	Pseudeurotium zonatum	Species	Pseudeurotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28601	Aspergillus falconensis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15160	Gutierrezia lucida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14043	Caulerpa serrulata	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Fruits	n.a.		Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Seed Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Seed	n.a.	n.a.	Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Leaf	n.a.	n.a.	Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Fruit Juice	n.a.	n.a.	Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Fruit	n.a.	n.a.	Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Bulb	n.a.	n.a.	Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.		n.a.	n.a.	Database[FooDB]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15442	Magnolia sieboldii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14673	Lathyrus nissolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2458	Aconitum violaceum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO15442	Magnolia sieboldii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10191	Ormosia balansae	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15626	Alternaria japonica	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13477	Cyberlindnera jadinii	Species	Phaffomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13311	Agelas linnaei	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11128	Ratibida mexicana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11912	Peltogyne porphyrocardia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15253	Helichrysum graveolens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6347	Iryanthera paraensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13160	Garcinia xipshuanbannaensis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15160	Gutierrezia lucida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4512	Fagraea gracilipes	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3244	Ascidia ahodori	Species	Ascidiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO7713	Euplotes raikovi	Species	Euplotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO965	Bleekeria vitiensis	Species	Plesiopidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2458	Aconitum violaceum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15442	Magnolia sieboldii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14043	Caulerpa serrulata	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10887	Pseudeurotium zonatum	Species	Pseudeurotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3949	Ceramium rubrum	Species	Ceramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12982	Dysidea amblia	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28601	Aspergillus falconensis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9860.1	Pinus brutia var. eldarica	Varieties	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14284	Delphinium shawurense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14673	Lathyrus nissolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12756	Roboastra tigris	Species	Polyceridae	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 NPC137887 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	26067
0.1-0.2	21944
0.2-0.3	1591
0.3-0.4	127
0.4-0.5	44
0.5-0.6	38
0.6-0.7	26
0.7-0.8	0
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9815	High Similarity	NPC96576
0.8333	Intermediate Similarity	NPC246202
0.8333	Intermediate Similarity	NPC224161
0.8333	Intermediate Similarity	NPC46335
0.8333	Intermediate Similarity	NPC279406
0.8333	Intermediate Similarity	NPC486519
0.8167	Intermediate Similarity	NPC58190
0.8167	Intermediate Similarity	NPC108811
0.8167	Intermediate Similarity	NPC170103
0.8167	Intermediate Similarity	NPC236202
0.8167	Intermediate Similarity	NPC262911
0.8167	Intermediate Similarity	NPC202742
0.7463	Intermediate Similarity	NPC278548
0.7424	Intermediate Similarity	NPC601997
0.7424	Intermediate Similarity	NPC609211
0.7424	Intermediate Similarity	NPC610665
0.7313	Intermediate Similarity	NPC600630
0.7313	Intermediate Similarity	NPC607896
0.7313	Intermediate Similarity	NPC611369
0.7164	Intermediate Similarity	NPC211561
0.6957	Remote Similarity	NPC65333
0.6912	Remote Similarity	NPC226809
0.6786	Remote Similarity	NPC268266
0.6786	Remote Similarity	NPC42760
0.6786	Remote Similarity	NPC220825
0.6786	Remote Similarity	NPC268342
0.6716	Remote Similarity	NPC313116
0.6716	Remote Similarity	NPC603340
0.6522	Remote Similarity	NPC70409
0.6522	Remote Similarity	NPC204770
0.6522	Remote Similarity	NPC600551
0.6522	Remote Similarity	NPC601980
0.6522	Remote Similarity	NPC602065
0.6522	Remote Similarity	NPC611024
0.6515	Remote Similarity	NPC601999
0.641	Remote Similarity	NPC212614
0.641	Remote Similarity	NPC205613
0.6364	Remote Similarity	NPC86630
0.6316	Remote Similarity	NPC147743
0.6316	Remote Similarity	NPC4809
0.6316	Remote Similarity	NPC73517
0.6282	Remote Similarity	NPC106601
0.6282	Remote Similarity	NPC151474
0.6176	Remote Similarity	NPC294558
0.6176	Remote Similarity	NPC18185
0.6176	Remote Similarity	NPC263940
0.5976	Remote Similarity	NPC159526
0.5921	Remote Similarity	NPC135021
0.5797	Remote Similarity	NPC277331
0.5797	Remote Similarity	NPC100482
0.5781	Remote Similarity	NPC178054
0.5733	Remote Similarity	NPC44192
0.56	Remote Similarity	NPC302549
0.55	Remote Similarity	NPC9309
0.5488	Remote Similarity	NPC78074
0.5484	Remote Similarity	NPC261619
0.5484	Remote Similarity	NPC61477
0.5484	Remote Similarity	NPC78770
0.5484	Remote Similarity	NPC219876
0.5484	Remote Similarity	NPC126029
0.5484	Remote Similarity	NPC15658
0.5455	Remote Similarity	NPC20050
0.5417	Remote Similarity	NPC184245
0.5417	Remote Similarity	NPC187801
0.5417	Remote Similarity	NPC610920
0.5385	Remote Similarity	NPC306267
0.5301	Remote Similarity	NPC478340
0.5263	Remote Similarity	NPC272552
0.5263	Remote Similarity	NPC226108
0.5263	Remote Similarity	NPC322899
0.5238	Remote Similarity	NPC478337
0.5238	Remote Similarity	NPC47398
0.5238	Remote Similarity	NPC478338
0.5238	Remote Similarity	NPC234333
0.5238	Remote Similarity	NPC260898
0.5195	Remote Similarity	NPC46283
0.5195	Remote Similarity	NPC469944
0.519	Remote Similarity	NPC478616
0.519	Remote Similarity	NPC478339
0.5161	Remote Similarity	NPC207179
0.5161	Remote Similarity	NPC167571
0.5161	Remote Similarity	NPC278552
0.5114	Remote Similarity	NPC478617
0.5067	Remote Similarity	NPC155564

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC137887 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5803
0.1-0.2	3325
0.2-0.3	13
0.3-0.4	5
0.4-0.5	2
0.5-0.6	2
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
0.5484	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.5484	Remote Similarity	NPD1613	Phase 4

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