NPASS Compound

Natural Product: NPC41764

Natural Product ID	NPC41764
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LCIQFCBYTOZSAR-BJSURHQRSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	21606550
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins [CHEMONTID:0001687] Cucurbitacin glycosides

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 105111 0 0 0 0 0 0 0 0999 V2000 -4.5302 3.3349 -0.1579 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4113 1.9147 -0.6512 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7910 1.3030 -0.5458 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8172 -0.1447 -0.9388 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.1488 -0.7001 -0.4391 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4374 -2.0668 -0.9581 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5839 -2.1470 -2.4448 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7673 -2.5032 -0.3539 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5028 -3.0179 -0.5666 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1462 -0.7668 0.9840 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0554 -0.1024 1.7817 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9270 0.5958 1.1936 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0713 -0.1574 3.2609 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7538 -0.8727 -0.5915 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6774 -0.3812 -0.0269 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4704 1.0667 0.1629 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0246 1.3396 -0.1005 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7846 1.9886 -1.4445 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2914 2.1165 0.9237 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1546 1.7998 1.0797 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7926 0.9312 0.0728 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9540 1.6035 -0.7338 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1854 0.5501 0.2582 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9358 0.8732 1.5434 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9547 -0.1644 1.8832 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9124 -0.4867 0.7572 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1170 -0.8889 -0.4577 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5867 -0.1225 -1.6436 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3808 -2.3771 -0.7365 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6346 -0.7725 -0.2099 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8720 -1.2191 -1.4224 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4260 -1.3578 -0.9380 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0855 0.0499 -0.7300 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4116 -0.0588 -0.0844 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2626 -0.6419 1.2722 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4502 -0.7883 -0.8225 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4313 -1.5110 -1.7763 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7489 0.6071 0.5430 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0330 0.2392 0.9176 C 0 0 1 0 0 0 0 0 0 0 0 0 8.0871 0.4670 -0.1073 C 0 0 1 0 0 0 0 0 0 0 0 0 9.4004 -0.0569 0.4310 C 0 0 2 0 0 0 0 0 0 0 0 0 9.6541 0.2554 1.8640 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3967 0.3380 2.6945 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3863 1.0378 2.0361 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4076 -0.8174 2.3936 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4107 0.5345 -0.3270 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7932 -0.3360 -1.2259 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8077 3.6119 0.6088 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5444 3.5505 0.2943 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5011 4.0375 -1.0446 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1445 1.8691 -1.7367 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4948 1.8896 -1.1602 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1112 1.4165 0.5185 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9042 -0.1596 -2.0634 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9899 -0.0398 -0.7253 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7059 -3.2427 -2.6908 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6641 -1.8323 -2.9442 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4986 -1.6138 -2.8024 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6238 -2.1396 -0.9298 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8467 -2.1770 0.7117 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7848 -3.6311 -0.2965 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3842 -3.7490 -1.2172 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1199 0.9037 3.6341 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9210 -0.7557 3.6396 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0896 -0.5642 3.5786 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5233 -0.8738 0.9802 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6549 1.3595 1.2400 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9807 1.3413 -2.2966 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7404 2.4044 -1.4193 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4246 2.9197 -1.4640 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4490 3.2099 0.6681 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8704 2.0108 1.8914 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6984 2.7950 1.1372 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2855 1.4247 2.1421 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8946 1.4989 -1.8060 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2297 2.6373 -0.4041 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3957 1.9000 1.4919 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2369 0.9240 2.4048 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4913 -1.0857 2.2615 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5630 0.2437 2.7311 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4967 -1.3712 1.1529 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1387 0.8102 -1.3885 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7861 0.1512 -2.3591 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2917 -0.7507 -2.2656 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6436 -3.0166 -0.2197 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3800 -2.6479 -0.3208 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4373 -2.5731 -1.8281 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4001 -1.5254 0.5990 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1723 -2.1925 -1.8137 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8535 -0.5037 -2.2443 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1192 -1.8219 -1.7802 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4104 -1.9831 -0.0479 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1989 0.4728 -1.7730 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7588 -0.0803 2.0744 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1769 -0.8359 1.5288 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -1.6915 1.2700 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0808 -0.7942 1.2743 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1871 1.5282 -0.4153 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4577 -1.1591 0.2366 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2391 1.1762 2.0420 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6556 0.8337 3.6468 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9796 -0.6713 2.9115 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8560 -1.3123 1.6643 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5999 1.4646 0.0120 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4684 -0.0772 -1.9291 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 6 9 1 0 5 10 1 0 10 11 1 0 11 12 2 0 11 13 1 0 4 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 6 17 19 1 0 19 20 1 0 21 20 1 1 21 22 1 0 23 22 1 6 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 27 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 1 34 36 1 0 36 37 2 0 26 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 42 45 1 0 41 46 1 0 40 47 1 0 16 2 1 0 34 17 1 0 44 39 1 0 36 15 1 0 33 21 1 0 23 21 1 0 30 23 1 0 1 48 1 0 1 49 1 0 1 50 1 0 2 51 1 6 3 52 1 0 3 53 1 0 4 54 1 6 5 55 1 1 7 56 1 0 7 57 1 0 7 58 1 0 8 59 1 0 8 60 1 0 8 61 1 0 9 62 1 0 13 63 1 0 13 64 1 0 13 65 1 0 15 66 1 1 16 67 1 1 18 68 1 0 18 69 1 0 18 70 1 0 19 71 1 0 19 72 1 0 20 73 1 0 20 74 1 0 22 75 1 0 22 76 1 0 24 77 1 0 24 78 1 0 25 79 1 0 25 80 1 0 26 81 1 1 28 82 1 0 28 83 1 0 28 84 1 0 29 85 1 0 29 86 1 0 29 87 1 0 30 88 1 1 31 89 1 0 31 90 1 0 32 91 1 0 32 92 1 0 33 93 1 6 35 94 1 0 35 95 1 0 35 96 1 0 39 97 1 1 40 98 1 6 41 99 1 1 42100 1 6 43101 1 0 43102 1 0 45103 1 0 46104 1 0 47105 1 0 M END

Standard InCHIKey	LCIQFCBYTOZSAR-BJSURHQRSA-N
Standard InCHI	InChI=1S/C37H58O10/c1-18-15-21(30(33(5,6)43)45-19(2)38)46-28-25(18)34(7)13-14-37-17-36(37)12-11-24(47-31-27(41)26(40)20(39)16-44-31)32(3,4)22(36)9-10-23(37)35(34,8)29(28)42/h18,20-28,30-31,39-41,43H,9-17H2,1-8H3/t18-,20-,21-,22+,23+,24+,25+,26+,27-,28-,30+,31+,34-,35-,36-,37+/m1/s1
SMILES	C[C@@H]1C[C@H]([C@@H](C(C)(C)O)OC(=O)C)O[C@@H]2[C@H]1[C@@]1(C)CC[C@]34C[C@]54CC[C@@H](C(C)(C)[C@@H]5CC[C@H]3[C@]1(C)C2=O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	662.4	Volume:	671.242 ? Van der Waals volume.
Dense:	0.987	LogP:	1.16 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.734 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.305 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	35.0
TPSA:	151.98 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	4.0	Rings:	7.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.254	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.439	Fsp³:	0.946
MCE-18:	195.806 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.984	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? 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:	0.142	Promiscuous compounds:	0.356

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.451	MDCK Permeability:	-5.059
Pgp-inhibitor:	0.052	Pgp-substrate:	0.479
PAMPA:	0.96 ? 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):	0.0
20% Bioavailability (F20%):	0.008	30% Bioavailability (F30%):	0.118
50% Bioavailability (F50%):	0.944

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.02
Plasma Protein Binding (PPB):	63.714%	Volume Distribution (VD):	-0.42
Fu:	35.826% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.191
BSEP inhibitor:	0.91

ADMET: Metabolism

CYP1A2-inhibitor:	0.007	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.021	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.554
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.583
HLM stability:	0.019 ? 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):

3.392

Half-life (T1/2):

1.737

ADMET: Toxicity

hERG Blockers:	0.016	hERG Blockers (10um):	0.056
Human Hepatotoxicity (H-HT):	0.538	Drug-induced Liver Injury (DILI):	0.139
AMES Toxicity:	0.832	Rat Oral Acute Toxicity:	0.121
Maximum Recommended Daily Dose:	0.123	Skin Sensitization:	0.995
Carcinogencity:	0.429	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.018
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.959
Hematotoxicity:	0.441	Drug-induced Nephrotoxicity:	0.85
Genotoxicity:	0.7	RPMI-8226 Immunitoxicity:	0.119
A549 Cytotoxicity:	0.151	Hek293 Cytotoxicity:	0.16
BCF:	1.831 ? 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:	4.612 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.07 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.433 ? 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
NPO21656	Pholidota yunnanensis	Species	Orchidaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16394543]
NPO22504	Tovomita longifolia	Species	Clusiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16562847]
NPO20204	Tephrosia candida	Species	Fabaceae	Eukaryota	aerial parts	Limbe (South West) Province, Cameroon	2007-APR	PMID[21510635]
NPO20204	Tephrosia candida	Species	Fabaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21510635]
NPO4213	Dicranopteris linearis	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20898	Agaricus bisporus	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20204	Tephrosia candida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23102	Siphonaria pectinata	Species	Siphonariidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26301	Acanthopanax brachypus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22374	Anomala albopilosa	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20024	Antennaria cana	Species	Carabidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19967	Calophyllum tomentosum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21417	Cortinarius evernius	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22504	Tovomita longifolia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21346	Eriocaulon buergerianum	Species	Eriocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22959	Eriococcus coriaceus	Species	Eriococcidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22633	Ganoderma carnosum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22442	Helix pomatia	Species	Helicidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21855	Hydrallmania falcata	Species	Sertulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13770	Neurospora santi-florii	Species	Sordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20459	Pfaffia pulverulenta	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21656	Pholidota yunnanensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22702	Phytolacca dioica	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22310	Pseudodistoma obscurum	Species	Pseudodistomidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20970	Salvia melissodora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21987	Senecio hygrophilus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20898	Agaricus bisporus	Species	Agaricaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO20898	Agaricus bisporus	Species	Agaricaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20898	Agaricus bisporus	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19967	Calophyllum tomentosum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21656	Pholidota yunnanensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20898	Agaricus bisporus	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21656	Pholidota yunnanensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21346	Eriocaulon buergerianum	Species	Eriocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19967	Calophyllum tomentosum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22702	Phytolacca dioica	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20898	Agaricus bisporus	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21346	Eriocaulon buergerianum	Species	Eriocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21346	Eriocaulon buergerianum	Species	Eriocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22702	Phytolacca dioica	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22310	Pseudodistoma obscurum	Species	Pseudodistomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4213	Dicranopteris linearis	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22633	Ganoderma carnosum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20024	Antennaria cana	Species	Carabidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20204	Tephrosia candida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21346	Eriocaulon buergerianum	Species	Eriocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21417	Cortinarius evernius	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21855	Hydrallmania falcata	Species	Sertulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26301	Acanthopanax brachypus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20459	Pfaffia pulverulenta	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21656	Pholidota yunnanensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23102	Siphonaria pectinata	Species	Siphonariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20898	Agaricus bisporus	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19967	Calophyllum tomentosum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22959	Eriococcus coriaceus	Species	Eriococcidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22374	Anomala albopilosa	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13770	Neurospora santi-florii	Species	Sordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22442	Helix pomatia	Species	Helicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20970	Salvia melissodora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21987	Senecio hygrophilus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22504	Tovomita longifolia	Species	Clusiaceae	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 NPC41764 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	21336
0.1-0.2	24957
0.2-0.3	3388
0.3-0.4	132
0.4-0.5	31
0.5-0.6	14
0.6-0.7	1
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	Natural Product ID
0.6829	Remote Similarity	NPC92299
0.593	Remote Similarity	NPC227879
0.593	Remote Similarity	NPC208333
0.5814	Remote Similarity	NPC470028
0.5556	Remote Similarity	NPC476512
0.5495	Remote Similarity	NPC470029
0.5435	Remote Similarity	NPC134967
0.5435	Remote Similarity	NPC476839
0.5435	Remote Similarity	NPC476838
0.5368	Remote Similarity	NPC89253
0.5281	Remote Similarity	NPC476513
0.5222	Remote Similarity	NPC478630
0.5165	Remote Similarity	NPC233649
0.5161	Remote Similarity	NPC472079
0.5109	Remote Similarity	NPC476510

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC41764 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6960
0.1-0.2	2148
0.2-0.3	42
0.3-0.4	0
0.4-0.5	0
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